Methyl 2-(3-nitropyridin-2-yloxy)acetate → 3-Amino-2-(methoxycarbonyl)methoxypyridine

HRID 1241301Notes

Reaction equation

HRID 1241301 reaction equation
[CH3:1][O:2][C:3]([CH2:5][O:6][C:7]1[C:12]([N+:13]([O-])=O)=[CH:11][CH:10]=[CH:9][N:8]=1)=[O:4]>[Pt]=O.C(O)C>[NH2:13][C:12]1[C:7]([O:6][CH2:5][C:3]([O:2][CH3:1])=[O:4])=[N:8][CH:9]=[CH:10][CH:11]=1

Participants

4

Reactant 1

HCID 12115511Methyl 2-(3-nitropyridin-2-yloxy)acetate

Product 1

HCID 121155123-Amino-2-(methoxycarbonyl)methoxypyridineYield 85.4%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 702EthanolSolvent

Procedure

A mixture of 0.3 g of 2-(methoxycarbonyl)methoxy-3-nitropyridine, 20 mg of platinum oxide, and 1.4 ml of ethanol was stirred at room temperature under an atmosphere of hydrogen gas for 3 hours. The gas in the atmosphere on the reaction system was replaced with nitrogen gas, and the reaction mixture was filtered through Celite. The filtrate was concentrated. The residue was subjected to silica gel column chromatography to give 0.22 g of 3-amino-2-(methoxycarbonyl)methoxypyridine.

Workup

  1. filtrationthe reaction mixture was filtered through Celite
  2. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-cce19d89b47b49fc82835d830bbf5d52
Source dataset
uspto-grants-2006_10
Patent number
US07115544B2

Reaction notes

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